3-[4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid tert-butyl ester

Base Information

• Chemical Name: 3-[4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid tert-butyl ester
• CAS No.: 185553-39-3
• Molecular Formula: C₄₉H₄₆NO₇P
• Molecular Weight: 791.88

Synonyms:3-[4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid tert-butyl ester

Chemical Property of 3-[4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid tert-butyl ester

Chemical Property:

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Technology Process of 3-[4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid tert-butyl ester

There total 5 articles about 3-[4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

(tert-Butoxycarbonylmethylene)triphenylphosphorane (86302-43-4,35000-38-5) + (S)-2-Benzyloxycarbonylamino-3-(4-chlorocarbonyl-phenyl)-propionic acid benzyl ester → 3-[4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ5-phosphanylidene)-propionic acid tert-butyl ester (185553-39-3)

Guidance literature:

With benzenesulfonamide; In toluene;

DOI:10.1016/0040-4039(96)01978-8

Reference yield:

benzyl N-carbobenzyloxy-L-tyrosine (5513-40-6) → 3-[4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ5-phosphanylidene)-propionic acid tert-butyl ester (185553-39-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / Et₃N / CH₂Cl₂

2: 91 percent / Pd(OAc)2, (Ph₂PCH₂)2CH₂, Et₃N

3: 75 percent / 1M n-Bu₄NF, 4 Angstroem mol. sieves / tetrahydrofuran

4: (COCl)2, DMF / toluene

5: 80 percent / BSA / toluene

With benzenesulfonamide; palladium diacetate; oxalyl dichloride; 4 A molecular sieve; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/0040-4039(96)01978-8

Reference yield:

4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-benzoic acid 2-trimethylsilanyl-ethyl ester (185553-34-8) → 3-[4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ5-phosphanylidene)-propionic acid tert-butyl ester (185553-39-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / 1M n-Bu₄NF, 4 Angstroem mol. sieves / tetrahydrofuran

2: (COCl)2, DMF / toluene

3: 80 percent / BSA / toluene

With benzenesulfonamide; oxalyl dichloride; 4 A molecular sieve; tetrabutyl ammonium fluoride; N,N-dimethyl-formamide; In tetrahydrofuran; toluene;

DOI:10.1016/0040-4039(96)01978-8

upstream raw materials:

(tert-Butoxycarbonylmethylene)triphenylphosphorane

benzyl N-carbobenzyloxy-L-tyrosine

4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-benzoic acid 2-trimethylsilanyl-ethyl ester

4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-benzoic acid

Downstream raw materials:

3-{4-[(S)-2-Carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-phenyl}-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid tert-butyl ester

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